Vacation rentals in Shirley

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Top-rated vacation rentals in Shirley

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A bright living room area features a sectional sofa and a coffee table set on light carpet. A smart TV is positioned on a low stand, and natural light enters through a skylight. Decorative curtains frame the window, adding a touch of style.
Apartment in Medford
4.88 out of 5 average rating, 161 reviews

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Top guest favorite
An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.
Home in Shirley
4.98 out of 5 average rating, 226 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Guest favorite
A living area features a gray futon adorned with decorative pillows, complemented by a small coffee table. A red accent chair provides additional seating. Soft lighting from the ceiling enhances the space, while wall art depicts blooming flowers, contributing to a welcoming atmosphere.
Apartment in Patchogue
4.88 out of 5 average rating, 240 reviews

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

Top guest favorite
A modern living area features a dark sectional sofa accented by cushions and a stylish area rug. In the background, a dining space with four chairs and a kitchen area is visible. Natural light enters through multiple windows, creating a bright, inviting environment.
Apartment in Patchogue
4.97 out of 5 average rating, 170 reviews

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Guest favorite
A comfortable living area features a light-colored sofa facing a wall-mounted television. A small dining table with two chairs is positioned nearby. Natural light enters through a door leading to an exterior space, and wooden flooring complements the overall layout.
Apartment in Central Islip
4.96 out of 5 average rating, 109 reviews

Cozy studio w/ private entrance

Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area with a pull-out twin bed and seating - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

Guest favorite
A well-lit bedroom features a spacious bed with decorative bedding, positioned against a soft blue wall. Natural light enters through large windows, adorned with sheer curtains. A compact dresser stands nearby, and an elegant table lamp adds functionality to the cozy space.
Home in Holbrook
4.91 out of 5 average rating, 297 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Top guest favorite
A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.
Apartment in Shirley
4.95 out of 5 average rating, 136 reviews

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

Guest favorite
A cozy bedroom features a spacious bed layered with soft bedding and decorative pillows. Pendant lights hang on either side, illuminating the room. Simple wall art and round mirrors add visual interest to the neutral walls, while natural light filters through a sheer curtain.
Apartment in Medford
4.81 out of 5 average rating, 102 reviews

Blue apartment in Long Island, Ny

Welcome to our blue apartment a Peaceful, comfy one bedroom apartment suitable for 4 people. Private bedroom has a Queen size bed with comfy mattress and two small closets to keep your belongs. Living room has two twin comfy beds, tv and desk. Kitchenette is equipped with necessities for a quick meal and coffee maker. You can also enjoy the shared backyard with the fire pit. Keep in mind if you stay past our check out time you will be charge an extra night.

Top guest favorite
A spacious studio features a queen-sized bed with patterned bedding, flanked by bedside lamps. A small dining table with two chairs is positioned near a window, allowing for natural light. A wooden bench is placed at the foot of the bed, enhancing the room's functionality.
Guest suite in Stony Brook
4.8 out of 5 average rating, 678 reviews

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

Guest favorite
A well-maintained putting green is positioned in the front yard, surrounded by soft turf and bordered by gravel. Small flags are placed on the green, with nearby shrubs and trees adding to the outdoor landscape. The house is visible in the background.
Home in Shirley
4.94 out of 5 average rating, 162 reviews

Beach Waterview, 3 KING Beds, Golf Putting Green

Take it easy at this 3 story waterview beach home with a putting green and fire pit. The Bellport Bay is across the street. Shirley Beach: 0.4 mile walk Smith Point Beach: 1.8 miles Featuring: 3 luxurious KING beds 👑 (and 2 fulls) Watch Netflix, Disney+ on the 70" living room TV and 3 50" bedroom TVs Fully equiped kitchen/dining room Enjoy BBQ Grill, fire pit on premium soft turf Highspeed mesh WiFi, keyless entry.

Top guest favorite
A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.
Cottage in Patchogue
4.94 out of 5 average rating, 253 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Top guest favorite
A spacious room is presented with a full-size bed dressed in soft linens. A decorative painting is displayed above the bed. A dresser and a coffee station are visible, accompanied by a comfortable seating chair. Warm lighting is provided by bedside lamps.
Guest suite in Ronkonkoma
4.95 out of 5 average rating, 138 reviews

Charming “hotel inspired” Retreat

Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

Popular amenities for Shirley vacation rentals

When is the best time to visit Shirley?

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Avg. priceG$39,747 GYDG$35,564 GYDG$36,609 GYDG$38,074 GYDG$40,166 GYDG$43,095 GYDG$46,442 GYDG$52,090 GYDG$38,074 GYDG$40,793 GYDG$36,609 GYDG$39,747 GYD
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Frequently Asked Questions

  • What are the most popular amenities for Apartment Rentals in Shirley?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Shirley have free parking?

    Absolutely! We offer over 60 house rentals with free parking in Shirley. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Shirley have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Shirley. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Shirley?

    Four-legged friends are welcome in Shirley. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there family-friendly vacation rentals in Shirley?

    Shirley has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Shirley have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Shirley. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Shirley?

    Experience the best of Shirley with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Shirley vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Shirley, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there vacation rentals with a dedicated workspace in Shirley?

    Yes! Work meets play with ease at over 50 vacation rentals in Shirley featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Shirley have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Shirley. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Shirley

  • Total vacation rentals

    Explore 90 vacation rentals in Shirley

  • Nightly prices starting at

    Shirley vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,600 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Shirley vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shirley rentals

  • 4.9 Average rating

    Shirley stays are highly rated by guests—averaging 4.9 out of 5!

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